


Feels Like The First Time

by Safiyabat



Category: Supernatural
Genre: Canon Het Relationship, Exhibitionism, F/M, First Time, First Time Blow Jobs, First Time Bottoming, Foursome, John Winchester's A+ Parenting, Light Bondage, M/M, Multi, Panty Kink, Plucky Pennywhistles, Prostitution, Threesome, Voyeurism
Language: English
Status: Completed
Published: 2014-10-22
Updated: 2014-10-22
Packaged: 2018-02-22 02:59:54
Rating: Explicit
Warnings: Underage
Chapters: 7
Words: 21,880
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2492006
Author URL: https://archiveofourown.org/users/Safiyabat/pseuds/Safiyabat
Summary: <blockquote class="userstuff">
              <p>Sam and Dean have had a lot of first times.  Some things were similar, some were vastly different.  Mostly set pre-series, with one scene set post Mark of Cain.</p>
            </blockquote>





	1. Kiss

**Author's Note:**

> This was written in response to a prompt on spnkink-meme over on LJ:
> 
> I really need Sam and Dean's firsts.  
> First kisses, first blow job(given and received), first time topping and bottoming, first time doing something kinky, all of them!  
> I'd prefer it if they weren't together at all, I just want to see them side by side.  
> Bonus points if they both had their firsts with the same person!(maybe an older boy like Castiel or Gabriel?)
> 
> I'm not very comfortable writing sexually graphic material, so I decided to take this prompt on to kind of force myself to work through that. 
> 
> I really want to thank my beta, Elwarre, who put a lot of time and energy into making this readable.

The first time Dean kissed anyone – romantically, sexually, not just in a putting-Sammy-to-bed kind of way – was when he was sixteen. This often surprises people, or it would if he talked about it with anyone. At all. Ever. They’d think he was a late bloomer, a blushing virgin, an innocent creature thrust into the brutal and often corrupt world of hunting only to be slowly worn away and tarnished or something when nothing could be further from the truth. Fact is, Dean’s interest in sex found an early outlet, but not all sex involves sweetness or gentleness, and Dean’s earliest sexual experiments were more of the hey-let’s-kill-some-time variety than the let’s-share-our-love variety. He was a hunter, after all. He was always going to be a hunter, and a hunter didn’t have time for any of that cutesy, lovey-dovey crap. 

Then Dad had abandoned him at Sonny’s, and even though he’d tried for a while to hold onto what he knew to be true, eventually his mind started to open up in spite of him. Maybe there was another way. Maybe Dad was just going to leave him here, maybe his dad didn’t need him after all. Maybe he could relax into a real life, a normal life. A life where he could form attachments, build relationships.

Of course that was when he met Robin, and over the course of weeks he’d fallen completely, head over heels in love with her. 

Their kiss, delightful as it was, reflected everything about his experience at Sonny’s. It terrified him – here he was, sixteen years old and able to kill fifteen different types of monster with basic household implements, and he knew how to make her scream for mercy, but the thought of hurting her, of scaring her, made his hands shake. And – and he had no idea what he was doing. He knew what to do with his mouth in other ways, and he wanted to kiss her, to taste her mouth and just make her smile right now, but he had no idea. Just like he wanted to use his brain and bring that B in English up to an A, but he had no clue how to write a decent essay that didn’t include twenty F-bombs without Sammy’s help. 

But here, here he had Robin. And she, she was able to put her hands on him and take control of the kiss. She knew it was his first kiss, and even if she didn’t know why it was his first kiss, even if she drew all the wrong conclusions about how he’d made it to sixteen with the kind of toughness he had about him without ever touching his lips to someone else’s, she was willing to show him what all the fuss was about. She tasted like strawberry lip gloss, and a little bit like whipped cream, and maybe like… a little bit like pumpkin pie? He never wanted it to end. 

He invited her to the dance, which turned out to be the biggest mistake of his life. Dean never got very into kissing after that.

*

Sam’s first kiss was Amy, and in later years he would reflect with a combination of bitterness and wry humor about how it figured that the first person to want to kiss him (and the first person he wanted to kiss) was not human. The universe had given him a sign; perhaps he should have listened. There had been other giant flashing neon signs for the future too, if he’d just been perceptive enough to read them. There was the fact that the girl had been not only not human, but a kitsune – the daughter of the creature his father and brother were hunting. If that wasn’t a metaphor for the life of Sam Winchester he didn’t know what was. There was the fact that she’d asked him to run with her – to leave, to flee hunting and Dad and everything the life represented – but in the end he couldn’t do it. He knew where that would lead. And he knew that no one could clean her out of the crime scene the way he could. So he stayed behind, covering for his early love and never, ever breathing a word to his family. 

He’d asked Dean for help. That was the funniest thing about it. He’d been crushing on her so he’d gone to Mr. Womanizer for help, because with the number of times Dean had kicked him out of this motel room or that studio apartment (or, on one memorable occasion, the Impala) he probably knew something about attracting a wide variety of women and because older brothers made up for all the weird smells and hogging all the hot water by offering advice to younger brothers based on having lived through things so you didn’t have to. 

And of course Dean’s plan didn’t work, because Amy was the kind of girl who wouldn’t have given Dean the time of day in a trillion years. Sticking up for her and treating her like a person, both being freaks – that had worked. It had worked better than Sam could have ever hoped, and he could never, ever let Dean know. Not once.

Oh, but that combination of adrenaline and bravado and the heady excitement of meeting someone – anyone – who could relate to your experience. Someone whose family life was as shitty as yours, someone who wanted out as badly as you did. Someone who could make you feel that maybe being a freak wasn’t as bad as it seemed, if you weren’t the only one. He hadn’t even hesitated, he’d just brought their lips together, and she’d responded eagerly. He guessed that she was every bit as isolated as he was, but he absolutely wallowed in the taste of her mouth. She tasted like Coke, like fresh meat, like the forest and electricity. 

And then it had all come crashing down. Of course it had. Everything did eventually. But he’d had that, even for a little while – a companion, someone who cared for him, who didn’t care that he was a freak. Someone who wanted him with them, instead of dragging him along. And Amy – she’d lived, she’d gotten away, and Dad and Dean had never even known she’d been there at all. 

He hated letting Dean think he’d struck out with the girl he’d asked about, but he consoled himself with the fact that Amy had lived. That was his secret, a victory to which he’d at least contributed and that neither Dad nor Dean could take away. And that kiss – there had been nothing quite like it. Whatever happened in his future sexual adventures, Sam would always find he enjoyed kissing most.


	2. Suck

The first time Dean ever felt the sensation of someone else’s mouth on his dick he was fourteen. He didn’t go into it looking for sex, nothing like it. He was just bored, didn’t want to go to his eighth-grade US history class and there was the concession stand out by the baseball field. No one was out there, it was as good a place as any to hide out until the end of the school day with no one freaking bugging him. He didn’t think much beyond that – what was there to think? Knowing stupid crap about a bunch of dead white guys wasn’t going to help him gank a ghoul, and if it wasn’t going to help him he wasn’t going to waste more time on it than the law required. 

The sooner Sammy figured that out and got on board the happier they’d all be. 

The concession stand was locked, but it wasn’t like things like locks were exactly problems for anyone named Winchester. He took care of it in seconds without even leaving marks and surveyed the scene. It wasn’t terrible. He’d been in worse. They’d taken all the food and drinks out, of course. Couldn’t risk getting rats or raccoons or whatever in here, even Dean knew that. Fortunately he had a nice big bag of peanut M&Ms to get him through. He settled in with his Walkman and a magazine and hunkered down for the day, waiting for the school day to meander its way to a close.

It was maybe an hour later that Debbie Bruckner made her way out there. She wasn’t a stranger, he knew who she was. He’d seen her around school, maybe a year older than he was and hot like a ghost’s freshly torched bones. She didn’t scream when she saw him, she just gave this little knowing smile with those pretty pink lips. “Dean Winchester,” she greeted. “Well hello.” She probably meant to sound all sexy. To his fourteen year old self she had sounded sexy, very sexy. When he looked back with a more mature eye he would realize she just sounded like a fifteen year old who smoked too many cigarettes and maybe had a chest cold, but at the time it had the desired effect. 

“Debbie,” he swallowed. “Hi there.” 

“I guess class wasn’t doing it for you today, huh?”

“I’m not exactly a book learning kind of guy,” he admitted, hiding his copy of _Cat’s Cradle_ in his bookbag. “I’d rather work with my hands.” 

She fluttered her eyelashes at him. “I can give you something for your hands to work on.” 

Not a lot of guys, younger teenagers whose bodies are just learning to process arousal and hormones and an organ that makes their clothes fit differently every time the wind blows for crying out loud, are going to turn down an invitation like that. Dean Winchester was certainly not one of the rare few (although, he reflected even in that moment, Sam probably would have been.) “I can do that,” he gulped.

She let him touch, running his hands over her breasts and playing with her nipples like they were some kind of switch. It couldn’t have been much fun for her, but she responded to it with half-closed eyes and little groans and demands that he not stop. He did stop, though, moving his hands lower in favor of his mouth. Debbie seemed to like that even better. He petted her under her skirt, over her underwear, and then he dared slipping his fingers underneath the damp cotton to explore what he found underneath. That, she definitely liked and it wasn’t long before she finished, body clenching around his fingers and biting down on her hand so her cries wouldn’t bring the grounds crew. 

When she came back to herself enough to speak she turned to Dean. “That was fantastic,” she sighed happily. “I want to return the favor.” 

He blinked owlishly at her. “Um, okay.” His older self would castigate his younger self for his lack of articulation, but his still-older self would point out that a fourteen-year-old boy experiencing a major blood flow diversion from his brain can probably be forgiven a momentary lapse in vocabulary.

That was when Debbie opened his jeans and pulled both them and his boxers down to his knees, freeing his trapped cock. It sprang against his lower abdomen, angry and red and throbbing, and she licked her lips and met his eyes. And then she reached out with that pretty pink tongue, licked a stripe up the underside, swirled it around the crown like she was catching the drips of an ice cream cone and wrapped those perfect pink lips around his cock. 

Up until now the only companion Little Dean had ever known was his own right hand, and once a little bit of petting from Sue Dembowski five towns ago in the woods behind the school on a dare. (Sam had caught them at it and pronounced their actions to be “totally gross, Dean.”) This – this feeling, these sensations – went beyond anything that even his deepest fantasies had suggested. Nothing in the world had ever been as hot as Debbie’s mouth, nothing so wet. He knew what to do intellectually, of course. He’d read articles. He’d watched porn. He’d been through sex ed in seven states, thank you very much, and that didn’t even count states where “abstinence-only” was a thing. Knowing with his brain – which was firmly disconnected from the proceedings at this point – and knowing with his body were two different things. He found himself powerless to keep himself from thrusting up and into her mouth, although he tried. Having her hands on his hips helped, but there was only so much he could do. 

He didn’t last long. He remembered to tap her head so she could pull off in time to avoid the deluge that was his load, finishing him off by hand with a wicked little grin on her pretty little face. He splashed his release all over the walls of the concession stand, biting back a shout.

Afterward he pulled his pants back up and offered her some of his peanut M&Ms. She accepted. They chatted about which classes they were ditching and why they were ditching them, a conversation that was cut short when they heard the fire alarm sounding off from inside the school. If they didn’t get back to whichever class group they were supposed to be with there would be bigger trouble than just skipping class. 

Once the fire trucks showed up they knew that school was cancelled for the day. Dean walked Sammy home. He wasn’t surprised to find their father there when he got back, demanding that they be ready to leave by that night. They’d been there more than a month already; it was time to move on. But in the late nights, when he sometimes thought he might have a daughter that he’d know about, he thought about naming her Debbie.

*

The first time anyone put their mouth to Sam’s dick was in high school, out in Wisconsin. They were in this particular town, this particular school long enough for Sam to join some extracurriculars even though his father sneered and pointed out (repeatedly, and at great length) just how much he’d be letting everyone down in the end. Well whose fault was that then? If he’d just stay in one goddamn place long enough to let him finish out school it wouldn’t be an issue. Never mind that – if he’d just let Sam stay in one place long enough to finish out school, it wouldn’t be an issue. Then he’d be rid of Sam’s face (which caused a problem for him) and Sam’s “attitude” (whatever that meant, and which caused a problem for him) and Sam’s “selfish” need to not risk life and limb on revenge for someone he’d never even met (which was a huge problem for him), and everyone would be happy. 

Well, Sam would miss Dean. That wouldn’t make him all that happy. But he knew where he stood with Dean in relation to their dad. 

He forced the rage from his mind before he went into the math team meeting. You couldn’t solve complex math problems if you were busy being pissed. You couldn’t afford to have anything clouding your thinking. That was what he liked about math to be honest – even an unclean thing like him could brush against the purity, the perfection of math. Nothing could sully numbers. You either got the answer right or you didn’t. No one could decide that suddenly four plus four equaled six or something.

He sat down in the classroom where the meeting was, taking a seat near the back of the room and listening to their advisor talk about the upcoming meet against St. Polycarp on Saturday. Well, he half-listened. He wasn’t really here for rosters and crap, he was here for the stress relief that math provided and the way that the math team would look on his college applications. He wanted to know what he should prepare for and that was pretty much it. 

Until Wagner. Tom Wagner, captain of the soccer team who did math team in the off season because why the hell not? Because being tall, athletic and hot like Derek Jeter wasn’t enough, he had to be brilliant too. And of course, because this was Sam’s freaking life, he had a massive hate-on for Sam. He’d had a massive hate-on for Sam since the day Sam had started here, no matter how much Sam tried not to cause trouble or get in his way or anything. “You can’t be serious,” the team treasurer objected, pecs standing out against his shirt in a way that should have been a dress code violation. “You can’t put Winchester into six events – there’s seniors who’ve been on the team since freshman year who are only in one event! Winchester’s been here six weeks and you’re putting him into everything like he’s some kind of show pony!” 

Sam slunk down into his seat as all eyes turned toward him. “I’m putting Sam into these events because he can handle them, Tom,” Mr. Mueller pointed out in a reasonable tone. “You’re in five events yourself, there’s no need to be jealous.”

“I’m not jealous of Sam Winchester,” the junior insisted. “I just think it’s bullshit that you’re showing all this favoritism to some no-name kid from the sticks whose family tree doesn’t even branch when you’ve got better qualified kids –“ 

“Suck my dick, huh?” Sam exploded, rising to his feet. All conversation in the room – all movement in the room – came to a complete halt as he fought against the redness that threatened to overcome his vision. “You got a beef with me that’s fine – you’ve had it since day one. But you leave my family the fuck out of it. You don’t know a goddamn thing about my family.”

Hazel eyes met amber as the pair stared each other down across the classroom. Sam’s hands hung loosely at his sides, waiting for Wagner to make a move. No one else dared to breathe until Mr. Mueller finally spoke. “I think the two of you need to go take care of your differences. The roster stands; the two of you can go talk it out. Report back to me tomorrow morning.” 

Sam grabbed his things and stormed out of the room, Tom Wagner hot on his heels. “Miss Turley’s room,” the midfielder demanded. “She’s never here on Tuesdays. You’d know that if you were from here.”

Sam rolled his eyes but opened the classroom anyway. Hopefully the asshole wouldn’t realize that the door had been locked – it hadn’t taken Sam more than a second to pick it, not like the locks at this school were substantial anyway. If he did he didn’t say anything, which was a miracle in and of itself. Tom just pulled down the shade over the window in the door and set his bag carefully down beside the entry.

“The fuck is your problem with me, anyway?” Sam demanded, slamming his bag down a little more heavily on one of the desks than was necessary. “I’ve stayed out of your way, I haven’t done anything to you, I’ve tried to accommodate your irrational hatred of me. What the actual fuck?”

“This isn’t your town!” Wagner retorted. “Everything was fine until you showed up. Jimmy Park and Brie Thomas were duking it out for valedictorian and then bam! Sam Winchester shows up and throws off the grading curve and no one knows which way is up anymore. Everyone knew where they’d be in terms of the soccer team in the spring – who’d make varsity, who’d make JV, who’d have to go play golf or something – but bam! Sam Freaking Winchester again with your stupid long-ass legs, and I’m pretty sure you can bench-press a semi. You know how many guys have gotten a date in the past six weeks?” 

“Uh,” Sam blinked, turning his head a little to see if maybe a change in angle would make this conversation make a little more sense. “The ones who asked someone who was interested?” 

“Zero!” shouted Tom, leaning into his personal space in a way that should have made Sam very defensive. “Not one guy has gotten a date since you showed up! Because all the girls want to see which one of them you’re going to end up with. And so do all the guys.” 

“Bullshit.” Sam crossed his arms over his chest. “The girls are not interested in some drifter kid in patched up clothes, alright? So you can pack up your little dominance display. I’m not stealing your women. Not stealing your men.” 

“Sure you are, Winchester. You don’t know it, but you are.” He looked away and his shoulders sagged. “Those abs, those arms, that ass? hell, that hair? You think anyone can resist? You think –“

Sam shook his head. “Wait. You’re pissed off because you think I’m hot.” This wasn’t happening. It wasn’t happening because things like this just did not happen, especially not to Sam Winchester. They didn’t even happen in pornos very often, probably because they weren’t believable.

Tom scowled. “I can usually keep my worlds separate. Besides, you’re straight.” 

He snorted. “You know what happens when you assume, right?” 

His adversary – former adversary? – looked up, relaxing slightly. “Are you fucking with me right now?”

“I’m bi,” Sam insisted, pressing his hands to his chest. “I mean, my family doesn’t know, but I’m bi.”

“Oh.” Tom blinked slowly. “Oh.”

“So.” Sam took a deep, shaky breath. This was a lot bolder than he ever got, but the situation seemed to demand it. “You think I’m hot, even if it seems to piss you off. I think you’re hot.” 

Tom was a smart guy. That was a large part of his appeal. He stepped in and touched his lips to Sam’s. His kiss might have been a bit tentative, but the one Sam returned wasn’t and Tom responded enthusiastically. He backed Sam against the wall of the classroom, each teen getting more courageous and adventurous as their confidence grew. Their kisses grew into little nips along the jawline and down to the collarbone as they shed layers, giving Sam the opportunity to admire with less interference the pecs he’d only seen through a veil of cotton before. 

Tom lavished his body with attention, toying with his nipples like he’d gotten notes from someone about how to make Sam sit up and beg in three seconds flat before moving on to the abs he’d so admired before. That felt good – both the physical sensation of Tom’s tongue and mouth on him, marking his flesh and licking it clean, and the rush of someone admiring the body his father and brother were constantly deriding as being too weak, too spindly, too in need of more training and more strengthening and more muscle and just _more_. It seemed to be just fine for Tom, and that was at least as much of a turn-on as the marks Tom was leaving with his teeth.

Tom’s hands reached for his belt buckle. “Is this okay?” he asked. 

Sam nodded. “Yeah. Yeah, please.” He had no idea what Tom wanted to do, but by this point his cock was straining against the zipper and even the soft fabric of his briefs wasn’t enough to mitigate the discomfort.

Amber eyes looked up at him through long, thick lashes as Tom pulled his jeans and underwear down his thighs, just enough to free his trapped cock. It sprang free and he could have sobbed with relief if it weren’t for the downright hungry way the other male was looking at it. “Tom,” he groaned as his partner started out with little kitten licks, bursts of sensation that just served to make him even harder. 

Tom grinned up at him. “You’re a big boy, Sam,” he drawled. “I’ve got to get ready for the main event, right?”

“You’re trying to kill me.” Sam ran his fingers over his partner’s soft, close-cropped hair. “That’s been your plan all along.”

“Can you think of a better way to go?” He began to swirl his tongue just under the crown, making Sam bite the inside of cheek. “No,” he had to admit with a whimper. “No I can’t.” 

That Tom had done this before admitted of no doubt whatsoever. He knew exactly how to work the slit with his tongue to get the best reaction out of Sam, how to use his hand in sync with his mouth to cover what he couldn’t swallow, the other to play with Sam’s balls. Sam gave himself over to the feeling, loving the way Tom’s hot, wet mouth felt around his sensitive cock. All other thoughts – school, hunting, even Dad – fled from his mind in favor of the bliss engulfing him. 

It couldn’t last, of course. He was sixteen, still learning his own body. He tapped Tom on the head to let him know he was close but Tom just winked up at him and kept on going, swallowing every drop Sam had to give when he finally came. Sam returned the favor with a hand job for the moment, and treated him to pizza besides. (Dad and Dean were gone, off on yet another hunt.) The next day they showed up to Mr. Mueller’s classroom before school started together and reported that they had indeed worked out their differences and they shouldn’t be causing any more difficulties for the team. 

When they left Tom’s hand caressed Sam’s ass. He pretended that he didn’t hear the teacher’s muttered “Fucking finally.”


	3. Give It Away

Dean was eighteen the first time he gave a blowjob. It was in Deadwood, South Dakota, and it was the result of a poker game gone south.

Dean was a pretty good poker player. In fact, he was an amazing poker player. Everyone told him so, and they weren’t really wrong. He could beat the pants off Caleb or Jefferson or Travis any day of the week, and he usually cleaned up when he went to the casinos. Poker, though, in addition to being a game of statistics and averages and mathematics and probability is also a game of chance and sometimes – well, sometimes you lose.

He’d already lost big on poker before, that one time in the Catskills when Dad had left them with too little cash to get them through. He’d tried to take what Dad had left them and turn it into enough, and it had blown up in his face, and Dad had abandoned him for two months as punishment. The situation wasn’t much different this time – Dad had left him with Sammy, gone off on some kind of “lead” he wouldn’t talk about, and thrown exactly enough money for two weeks’ rent on the table. That had been a week and a half ago.

So Dean had taken the cash that was left, because they needed things like food, and gone out to find a poker game. Yeah he was good with Baby, but it wasn’t like he had any certifications or anything. Garages wanted that kind of thing if you were going to get a job as a mechanic these days. And it wasn’t like they were going to give you a job for a week or two. For all that his father had lost his mind when Dean had lost the money the last time he’d ensured that the only route available to him to get money was hustling so here he was. 

He’d done well at first, doubling their money quickly and then some. And then he’d bet big, hoping to get a little bit more to tide them over, and wound up losing it all to some rancher in shiny boots and a big hat. And Shiny Rancher Dude hadn’t been done yet, because when Dean got up to leave the table he put a hand on his. “Wait a minute, now,” he’d drawled. “No need to go running off. Why don’t you try to win it back?”

“I’m out,” Dean told him tersely.

“I’ve got a proposition for you,” the rancher offered. “You win, you get double your money back. I win, you give me a blow job.”

“Excuse me?” Dean felt his eyebrows rise, not quite sure he’d heard right.

“Aw, come on. What’ve you got to lose? It’s just a blow job, kid.” And he grinned. 

Dean thought about Sammy, finally starting to grow and of course choosing the most inconvenient time to do so. He thought about his father and how pissed he’d be about the money. He thought about the trade-off – enough money for the whole month’s rent, versus possibly having to do what he so enjoyed having done to himself. “Fine,” Dean replied. “I’m in.” And I’d better not lose, he added tersely to himself.

The hand went quickly. It was always going to go quickly, because Dean had a pair of twos. He might have gotten a worse hand if he tried, but he wasn’t sure how. “A couple of shots for my young friend here,” the rancher asked the waitress. “He’s going to need them.” 

Dean glowered, but he took the shots. He’d made the bet, he was going to live by its terms. When he’d downed the whiskey he turned to his companion. “All right,” he sighed. “How do you want to do this?” 

“Come on out to the parking lot,” the man smiled. “No one will care if we’re in my car.” 

The guy’s car turned out to be one of those massive Cadillac SUVs with the tinted windows. Dean grimaced as his companion climbed into the back seat, unzipped his jeans and spread out. “I’m guessing you’ve never done this before?” 

“No,” he had to admit. “I’m pretty good with my mouth if you’ve got, you know, breasts.” 

The gambler chuckled. “Relax. One blow job doesn’t turn you gay, kid. Just think about what you like the ladies to do to you, and if I want something different I’ll tell you, alright?” He’d taken off his hat. Dean could see vaguely salt-and-pepper hair with a mostly unlined face.

“Yeah.” The sooner Dean got through it the sooner he could get to figuring out a way to explain this to Dad. He took a deep breath, steeled himself and leaned in. 

Wow. This was… this was a guy. Guys weren’t supposed to think about other guys’ junk, not ever. There was porn, but that was different. It was porn. The guy in porn was there to do things to girls in porn, so you could imagine it was you doing things to girls in porn. He’d never been this close to another man’s dick before, not close enough to smell it. Close enough to taste it. This guy, he didn’t quite look the same as Dean. He was smaller, maybe a little thicker but maybe it just looked that way because it was shorter, and his hair was thick and wild. 

Dean reached out and touched the half-hard member, which jerked in response. The guy hissed. Was that a good noise or a bad noise? “Just think about what you like the ladies to do to you,” he’d instructed. Dean closed his eyes and tentatively licked it. Okay, that wasn’t so bad. How did he usually like this to go? He opened up his eyes and made contact with the man’s velvet-soft brown eyes, which had already started to glaze over, and let his tongue find the vein that ran up the underside of the penis. Yeah, that usually felt good for most guys, right? His tongue caught on the underside of the head, right where he knew a bunch of nerves was just begging to be toyed with. His companion groaned, a long, shuddery sound, and a drop of precome appeared at the slit. 

Right, the slit. Uh. He had to do something about that, right? He maintained eye contact with the guy while letting his tongue seek out that opening, and now he could see why so many girls complained about the taste. He wasn’t such a big fan himself. His gorge rose and his stomach threatened to rebel, but he didn’t back off. He’d made a bet and he was going to honor it. If his client’s hands grabbing his hair was any indication, he was doing a good job. 

Eventually he decided he’d done enough playing and got down to some serious suction. As serious as an untrained mouth could provide, anyway. This was vastly different on a guy, for obvious reasons, and it didn’t take much thrusting from Rancher Dude for his gag reflex to kick in. He remembered how girls usually took care of that with him and put his hands on the older man’s hips, stilling him, and bobbed his head up and down while adding an appreciative-sounding hum. 

The hum sent Rancher Dude over the edge and he spilled into Dean’s mouth and down his throat. Dean didn’t like that, not one bit, but he made sure he swallowed every last drop. He didn’t want to spill any on his own clothes and he didn’t want to be accused of not fulfilling his part of the bargain. And, in a very weird way that he’d never have confessed to even under torture, he was proud of it. If he was going to do a job he was going to do it right and he was going to do it well, and if that meant swallowing every drop of come that meant swallowing every drop. 

Rancher Guy leaned back, panting for a few moments before he collected himself. “Thank you,” he said, tucking himself back into his pants and reaching into his wallet. He pulled out a business card. “You are a talented young man, and if your hands are anything to go by you’re not afraid of a little hard work. My ranch is about an hour outside of town. If you’re looking to make some money I can always use some extra ranch hands, even on a casual basis. If you decide you want to make a little extra money while you’re there – well, there’s no obligation, but the door is open to you.” He grinned. 

Dean thanked him and told him he’d consider the job, and he went back to Sammy only to find that Sammy had parlayed the fifty bucks he’d held back from his poker game into two hundred at pool. He cuffed him for going into bars without him, without backup, but the money did help. 

Still, he went to Ed’s ranch the next day. A job was a job, after all.

*

Sam offered his first blow job when he was fifteen. The circumstances were maybe a little lacking since he’d been kidnapped by a weird gladiatorial cult. Maybe “kidnapped” wasn’t the right word, he had to admit as he was stripped down, issued a loincloth and put into a cell. His father had wanted this. Well, his father had put him out there as bait, since they’d been taking boys between fourteen and sixteen and leaving their corpses out in fields sometime later. Whether he wanted this specific fate for Sam was debatable but considering how apeshit his father went at the slightest hint of Sam escaping him he was fairly certain that Sam getting out via kidnapping by a strange gladiator cult was probably not in his game plan. 

Then again, maybe it was. Sam was learning more about the cult this way than the Winchesters ever had before, and his father had been desperate to gain intel on the enemy. They’d stripped him, they’d painted him all over with weird symbols that had nothing whatsoever to do with any pantheon he’d ever heard of, and they made him kneel in front of an altar while they prayed in Latin. Not in the Church Latin that obsessed his father, no – this was Classical Latin, so it took Sam a few minutes to adjust his vocabulary. Apparently the miscreants-of-the-week were a cult that had decided that the gladiatorial games needed to be re-created with the gladiators as a sacrifice to the Roman gods of the dead. They trained, they got prayed at, they got locked up in their cells. 

The training, such as it was, wasn’t bad. He’d had much worse in John Winchester’s Army, and if he wasn’t as practiced with a trident-and-net as he was with a knife or a shotgun he made up for it with speed and agility. The food, too, was better than he was used to. And for a couple of days he even had a cell to himself.

Then they added Josh to his cell. Well, the cell had two bunks, of course they would have added someone eventually. The guy had been a basketball player from two states away and had one of the nicest bodies Sam had ever seen on a high school kid. “What the hell, man?” Josh asked in a voice that only shook a little. 

Sam explained what he thought was going on, explained why. Josh gave a grin that combined lost and sexy in all kinds of weird ways. “Smart and hot. Too bad we’re all going to die.” 

“We’re going to find a way out of this, Josh. My family’s looking for us right now.”

“So are the feds, so what?”

“Yeah. But my family – they kind of specialize in this stuff.” 

By day they trained and at night they lay awake in their bunks, talking. Josh, too, was smart. He didn’t like their odds, but he was paying attention to the routines of the guards and the other prisoners. Some of the other kids had accepted their fate, begun to look forward to the arena. They started to act out against the other boys, taking their food, attacking them in the practice yard for no reason. Those boys were soon moved to another area. Part of Sam was glad of that, because he didn’t need the added hassle of watching his back. He truly loathed that part of him, since all of him knew they’d never see those boys again. Not alive. 

The first combat Sam saw in the arena was one week after his arrival. The captives from Sam’s group were all seated – in chains – on a bench in the front row. Cult members filled bleachers in a small indoor arena. The place looked for all the world like an indoor riding arena, like one you might see at a county fairgrounds. He watched as a boy he hadn’t seen before – now not even wearing the loincloth they’d been issued, just naked except for armor and the ritual paint with which their captors sometimes adorned them – strode into the center ring. Cultists applauded and cheered. Another boy – one Sam thought he’d seen in the first few days there – strode in after him, and the boys fought. 

The fight didn’t last long. The first boy was a champion, and he was a champion for a reason. The second boy could never have been in the arena before and he never would be again. The first boy jumped right on top of him, armed only with a dagger. The second boy might have had a net and a trident, but the net became useless once the first boy cut his artery and the nerves of his arm. The trident was only a useful weapon if you could keep enough distance between yourself and your opponent to use it. The second boy fell to the ground, hoping to get the first off of him. Sam could have told him that it was a bad idea. The first cut his throat then and there, and as the second jerked and bled the first bent down, bit in and tore out his throat. 

More than a few of the other boys chained to the bench with Sam threw up. Sam was not above joining them, although he managed to keep himself together. Josh did too, although he grabbed Sam’s hand and held it tightly. Sam did not let go. An eerie gray glow filled the arena for a moment before swirling into the ground and fading. 

That night Josh did not sleep in his own bunk. Sam felt his warm body slide in beside his own, underneath the threadbare blanket. “This okay?” the older boy demanded.

“More than,” he admitted, opening his mouth as Josh’ lips connected with his. 

The thing with the loincloths was that, well, there was no hiding anything. Lying here under the blanket kissing Josh felt good, what with the way that their bodies were pressed up together and all. It would have felt good even if it wasn’t a distraction from the misery of their daily lives and the horror of what they’d just witnessed. He couldn’t hide himself getting hard, and neither could Josh. 

Sam considered. He’d always known he wasn’t straight, but had Josh? For that matter, how okay with this was Josh right now? This might just be an any port in a storm kind of thing. Sam was okay with that on his part, but what about Josh? “I want to, uh… I’d like to suck your dick,” he whispered into his bunkmate’s ear. “Is that okay?”

He could hear a little laugh. “Christ, we could all die soon and you’re worried about a little blowjob?”

“Want to make sure you’re okay with it.” 

“I don’t think anyone’s ever going to say no, Sam.”

He moved the flimsy fabric of the garment aside and contemplated the dick before him. There wasn’t a lot of light in here, but he could feel it. The shaft was thick, impressively so. It wasn’t overly long, which was good for Sam right now, but it wasn’t short either and it had a little bit of a curve to the left. He considered his approach, trying to remember what he’d seen in the porn Dean was always watching.

Finally he just went for it. Josh was only a year at most older than he was; how much more experience could he possibly have? Josh groaned as he took the tip into his mouth, swirling his tongue around the crown and working the slit before inching his way down. There, that should work out okay, right? Josh’s hips started to buck, forcing his dick back into Sam’s throat. No, that wouldn’t work at all. If he was going to die here he was going to do it fighting, not on his knees sucking cock, even if he was finding that he kind of liked sucking cock. He tried to force his throat to relax. He could take it deeper if he could just relax. 

Josh gasped. “I- I’m close, Sam.” The younger boy knew Josh was trying to be a gentleman and give him fair warning, but Sam didn’t want to stop. He wanted to keep going, wanted to keep on hearing those noises and knowing that he’d caused them. He wanted to know what Josh’s come tasted like, which was probably a weird thing to want but he’d been kidnapped by a weird gladiator cult and was being kept prisoner dressed in a loincloth. Weird was relative at this point. 

Josh returned the favor with a hand job, and the next day they started quietly recruiting other kids to overthrow the cult. A week later they’d killed all of the cultists and Sam found the telephone. They waited for his father to come and clear them out of the crime scene, having agreed that no fed would believe the bit about the gods. 

Sam knew he’d never be allowed to have contact with Josh again.


	4. Get Down, Make Love

Dean experienced penetrative sex for the first time with Veronica Everett in eastern Oregon. He wasn’t entirely sure which town it was, they didn’t stay long enough to bother with things like enrolling in school or getting a real place to stay, but he remembered her name for the rest of his life. He was fifteen years old and he was at that stupid Plucky Pennywhistle’s place with Sammy, trying to keep him out of trouble while Dad was off doing something real and important and exciting. There he was, minding his own business playing skee-ball and collecting tickets in anticipation of a rainbow slinky just like he’d had before the fire when she walked by. Tall, legs for miles, C-cups at least and long, curly red hair. She glanced at him and winked and then kept carrying her tray right on into the kitchen. 

One of the kids watching him play skee-ball glanced at him. “Really? Veronica Everett? You think you’ve got a chance?”

His mind went back to the sway of her hips, the bounce of her curls, the wink of her wide blue eye. “Maybe. Why not?” 

“Because you just rolled into town or we’d have seen you before, that’s why,” the other kid scoffed. “You so don’t have a chance with a girl like Veronica Everett.” 

“Besides,” the first one said. “She’s a pro. She’ll eat you alive.” 

Dean snorted out his nose. “What would you know?” 

Of course Dad hadn’t come back for them by closing time. It was Veronica who approached him to point out that the place was closed, putting an arm around his waist. “Hi,” she purred right into his ear. “I’m really sorry, but we’re closing now.” 

He grimaced. “I know, but our dad hasn’t come to get us. He was supposed to, and I know he’ll be here soon –“ 

“Well.” She gave him a low, sultry smile. “As it happens, I’m off the clock. I know where we could go to kill some time while we wait.” 

He gave Sammy a glance. The kid was sitting near the door, clutching his backpack and looking about sixteen shades of white. He was probably just pissed that Dad was off saving lives instead of playing chauffeur. “Yeah. That would be fantastic.” 

She took him by the hand and led him to the ball pit. “Seriously?” he chuckled. 

“What? No one can see what we’re doing in here!” she pointed out mischievously, and before he knew it only her head was visible above the balls. “Why not?” 

He shook his head and dove in, burrowing his way under the plastic spheres until he was completely submerged as well. 

Veronica didn’t take long before her hands were up and under his shirts. “Hi there,” she purred. “Those are some nice pecs for a guy your size.” 

“Hey,” he objected. “I’m still growing.”

She scooted up so that she was sitting right on his lap, and damn if that didn’t feel good. “Why yes, yes you are.” She moaned lightly as his hand cupped her breast. “Oh, that’s nice. That’s really nice.” 

They groped around each other for a little while, until Dean slid his hand up her skirt and discovered that she’d misplaced an important part of her wardrobe. “Um, Veronica?” 

“Yeah?”

“You seem to have lost your underwear.”

“Oopsie.” 

He threw his head back and laughed as he let his fingers explore her body, loving the way she responded to his touch. This was what he liked about making out with girls. He liked the way they moaned when you found their clit, lavished it with attention. He liked how they felt when they came around your fingers. And some of them even liked it if you played a little bit around the back door there, just a little. It wasn’t a thing for all or even most of them, but it was definitely a thing for Veronica because she started rocking like a freaking granny’s chair. She grabbed his pants and pulled down, freeing his cock before finding a condom somewhere (seriously, where?) and rolling it onto him. “Uh, Veronica?”

“I want to ride you.” 

What exactly was he supposed to say to that? “Yes. Okay, fantastic.”

She straddled him, lined him up and sank down onto him with a shaking sigh. Dean lay back for a moment, content to let her set the rhythm before allowing his hips to rise up to meet her. 

The feeling, even through the condom, was indescribable. She was so hot he thought he might burn. When he did finally move he was met by the most incredible groan from her. “Oh, yes. Yes, just like that. Fantastic.” He moved his hand forward to tease her clit again – he’d seen that in a porno that hadn’t been hugely different from this scenario really – and she finished. 

He lasted for a few more thrusts before spilling into the condom with a groan. She collapsed down onto him for a moment and then dismounted. “That was amazing,” she sighed happily. 

“Yeah. I mean, it was fantastic for me too. I, uh, it was my first time.”

“Wow. We’ll have to do it again soon.” 

A throat cleared right near the ball pit, high and clear. “Uh, Dean? Dad’s here.” 

Dean sat bolt upright. “Shit! Sammy!” 

Veronica snickered. “See you soon, Dean.” 

Dad was there, and he made sure Dean washed up before he’d let him back into the Impala. Much to Dean’s surprise, he was willing to stay in the town an extra couple of days even though he’d finished the job he’d shown up for. Sam was less enthusiastic for once – he even cried, something he hadn’t done in front of their dad since he was all of what, five? – but their father was adamant. “Your brother deserves this, boy,” he insisted. “And you’re going to let him have it.”

*

The first time Sam had penetrative sex from the giving end he was seventeen years old, on a job with only his brother for supervision, and as usual Dean was trying to “help.” Sam rolled his eyes at Dean. “I don’t need you to ‘make a man of me,’” he told his brother. “I honestly can’t think of anything I’d rather do less than hit a brothel with my brother.”

“Why, Sammy?” Dean shot back. “Sex is a beautiful and natural act. It ain’t healthy for you to lock yourself away like a monk. You’re seventeen. You should be out there enjoying the pleasures that life has to offer.”

“You mean like a stable roof over our heads? Or knowing where my next meal is coming from? How about not dying before I’m twenty-four?” he shot back. He already knew full well what a beautiful and natural act sex was, thank you, and he did not need to discuss it with his brother.

“Yeah, well, those aren’t negotiable. And quit your bitching. We save lives, Sam.” 

“Lives that are apparently worth more than ours.” He turned his head. He shouldn’t pick this fight with Dean, he knew that he shouldn’t, but if it got him out of going to a brothel with his brother the sulkiness and resentment would all be worth it. 

“Look. You can’t get out of the parts of our life that you don’t like. It’s just not an option. But you can suck it up and try to enjoy something of what’s left to you.” Yeah, maybe this would work. He had the jaw clenching, the knuckles white around the steering wheel – if he could piss Dean off enough maybe this whole thing could be avoided. “We’re never going to settle down so you can find yourself a nice little wifey with a dog and a white picket fence and a yard. Deal with it.” 

“Maybe you’re not. Maybe you like the whole serial killer thing. Me? I’m getting out. And I’m not buying sex.”

“There’s nothing wrong with it, Sammy,” Dean groaned, banging his head against the headrest. “If they’re willing –“

“And you can’t prove that they are, that someone isn’t coercing them into this –“

“- And you can afford it then what the hell is your problem?” 

“My problem is that I don’t like casual sex, Dean! I like relationships. Interactions. I like sex when my partner knows my name and I know theirs and we actually engage more than once and we get to know different ways to turn each other on and actually freaking spend time with each other outside of bed!”

Dean shook his head. “Tough toenails. You can’t have that in this life. You get quick hookups.”

“And that’s why I’m getting out!”

“That’s just how you feel right now,” Dean told him with a tight, patronizing smile, and Sam sighed. Dean wasn’t going to budge. Neither was Sam.

They got to the house – an older place, it looked like pretty much any other house in a mixed-use neighborhood. “Don’t lose your phone,” Dean growled when Sam declined to enter. “I ain’t looking for your uptight, sorry ass. And you come running when I call you.” 

Sam just walked off, uninterested in his brother’s bad mood. He’d caused it, of course – all Dean had wanted to do was to congratulate himself on getting his little brother laid, and Sam had had to go and ruin it, like he ruined everything. Of course telling Dean he’d already had sex, he just liked bottoming – yeah, that wasn’t going to go over so well. He walked over to the town’s one bookstore, a sole proprietorship that mostly sold used books of whatever type happened to float in, and found a couple of books about Norse ritual that he hadn’t seen before.

“Are you pagan?” asked a woman in the aisle, looking up. 

“Huh? Oh, no. I’m just… I’m just interested in different cultures. Different mythologies, different rituals I guess.” He felt his cheeks go red. Explaining to civilians that he was looking for research material on how to kill mythological creatures would go over about as well as explaining to Dean that he liked taking it up the ass. 

“Oh. Yeah, me too.” She held up her own volumes. “This week it’s Aztec lore.” 

“You can probably skip that one,” he offered, pointing at the one in her left hand. “I’ve read it. Written entirely by a white guy with a fetish. Archaeology disproved everything he wrote down.” 

She glanced at it. “That’s actually kind of a relief.” She held out a hand. “I’m Arlene.”

“Sam.” They shook hands. “Are you local?”

“Just passing through. I’ve been here for about a week.” 

“Got here about a day ago. Just passing through myself though.” 

She grinned at him. “Well, since I’m at least more assimilated than you are why don’t you let me introduce you to the single best eatery in this two-stoplight town?” 

He laughed and let her lead on. The single best eatery in this two-stoplight town proved to be a little Mexican place run by someone who had to have been someone’s grandmother back when this state had still been part of Mexico, but the mole was perfect and you couldn’t ask for more than that. Afterward they walked around a little, talking about the “wonder” of the road. “Would it be astonishingly forward of me if I kissed you right now?” Arlene asked him as they stood under a streetlight.

He grinned. “Doesn’t mean you shouldn’t do it.” 

She pulled his face down and kissed him. With an intro like that he kind of expected a sweet or gentle kiss, especially given that she was older than he was by a good six or seven years at least. A gentle kiss would have been a proper way to be sweet to a young kid. What he got was heated, passionate. He couldn’t help but respond in kind. “We should move this indoors,” she whispered as she grabbed a handful of his hair.

He nodded as his body reacted. Part of the reason he fought so hard with his father about keeping his hair long was because of the way it felt when people tugged on it. “Yeah. Yeah, we should do that. Only – my brother has the car.” 

“We can go to my place,” she promised, and indicated the building they stood in front of. 

Her place turned out to be an efficiency apartment, not much different from one the Winchesters would rent. He didn’t get a chance to look around much because she was kissing him again as soon as the door was closed. “I need these off,” she told him, tugging at his shirts.

“I can do that.” He got rid of his outer shirt, then his tee shirt as quickly as he could. She’d divested herself of her own top garments as he did his, so that she stood facing him just as bare-chested as he. “You’re beautiful,” he told her, eyes stuck on the captive beads dangling from her nipples.

“Like these, do you?” she purred. He nodded. “They won’t break if you touch them, Sam.”

He laughed a little, bent down and took one nipple into his mouth. This he knew he could do, knew he was good with. She gave an appreciate little moan when he started that soon turned into a full-fledged groan of delight. He continued working her breasts, because every sigh or moan or groan was like pure praise to him. It meant he could do something right. 

She guided his hands down, placing them on the top button of her jeans. He met her eye. “Are you sure?” he asked her. 

“Oh God yes,” she insisted, taking a break from where she was admiring his abs. “Just… come on. Please.” 

He grinned. “Anything you say.” He helped her over to the bed, where the offending garments found their way into the pile of clothing. 

His cock pressed uncomfortably against his zipper but he ignored it in favor of the amazing woman spreading herself out in front of him. He liked this, liked it as much as he liked sucking cock and for a lot of the same reasons. He liked the fact that he got to see and hear and feel his partner’s growing arousal and ultimate release and he loved the fact that he got to be the cause of their bliss, even if it was only a momentary relief for them. He loved the fact that he – a person who had been deliberately isolated from people his entire life – got to be so intimate with another human being as to know what they tasted like, what they looked like in their most private moments, the scent of their arousal. It was different on women than it was on guys, of course, but ultimately Sam got the same thing out of it. 

And Arlene got a lot out of it too, if her cries were anything to go by. “I need you, Sam,” she gasped when she finally finished shuddering through the aftershocks and tugged him up closer to her face. “I need you in me.” 

He froze. “Are you sure?” he asked again. “I’ve never done that with a woman before. I don’t want you to –“ 

She drew back, disbelieving. “Seriously? A mouth and hands like that and you’ve never touched a woman before?” 

He laughed a little. “No. I’ve just never penetrated a woman before. I’ve had sex with guys but…” 

“But you usually bottom,” she surmised with a knowing smile. “I gotcha. Interesting. Well, do you want to have sex with me?”

“Yes,” he told her fervently. “Oh yes. I just don’t want you to be… you know. Dissatisfied.”

She laughed, reaching into the nightstand for a condom. “Sweetie, you’ve already more than satisfied me. Come on. You’re wearing too many clothes for this.” 

He had to agree. He peeled off his jeans and his briefs, jumping almost to the ceiling when his phone started to ring.

She looked at him. “Don’t you need to get that?” 

He considered it. “Nope. It’s my brother. He makes me wait around often enough.” 

She gave a cackle of delight, caught his chin in her hand and brought his face down for another kiss. He wondered if it was weird for her, tasting herself on him, but she didn’t seem to mind. He never objected when he tasted himself on his own partners, after all. His cock, which had begun to lose interest when Dean called, remembered where it was and why it was here. He checked Arlene. She was still wet, amazingly wet from before, wet and relaxed and ready for him. He checked the condom, because the last thing the world needed was more Winchesters running around. “You’re sure you’re okay?” he asked her again. She nodded. “How do you want to do this?” 

She pulled him on top of her and wrapped her legs tight around his waist. “That should be good for your first time,” she told him. “We can get more creative another time, if you’re game.” 

He lined up the head of his cock with the hot, wet space that seemed to call out for him and wondered if there was any possibility that he wouldn’t be “game.” 

She gasped when he breached her and for a moment he thought he might have hurt her, but she gripped his arm tight. “Do not stop,” she ordered. So he kept sliding in until he heard her cry out, and then he pulled back. “Yes,” she called. After a moment he figured out a rhythm – it wasn’t like he’d never done this before, it was just a different angle for him. And Arlene definitely seemed to enjoy what he was providing. Sam could feel the tight, hot walls of her body taking him in, engulfing him, welcoming him. He’d known he would like making love to a woman – he was attracted to them after all – but he hadn’t quite understood what it would feel like to be so completely surrounded like this. 

She came first, clutching him to herself as though she could draw him even deeper. He followed within seconds, spilling into the condom and collapsing down, forehead to hers. They lay together for a few moments just like that, sweaty and panting, before he pulled out and went to dispose of the condom. She was already half dressed by the time he returned, wearing her underwear and tee shirt. “You should probably see what your brother wanted,” she suggested with a grimace. “He called again while you were in there.” 

“Yeah,” he sighed. “I’ll do that.” He pulled his phone out of his pocket as he tried to step into his jeans. Funny how they felt much more awkward going on than they had coming off. 

He didn’t bother with voice mail, because Dean hadn’t left any. He just called his brother back. “Dude! Where the hell were you?” the elder Winchester seethed into the phone. “I just almost got arrested after I shook down a little old Mexican lady looking for you!” 

“She was born here, jackass,” Sam retorted with a sigh. “And I was busy.” 

“I told you to come running when I called for you!” Dean reminded him. 

“And I told you I was busy. Where are you?” 

He rolled his eyes at Arlene, who giggled.

“Who was that?” 

“A friend. Where are you, Dean? I can’t come meet you if you don’t tell me where you are.” 

Dean was silent for several seconds, and Sam could just see his brother staring at the phone in offended annoyance. “I’m outside that stupid bookstore I know you decided to go spend my money at,” he finally informed him. “And we’re going to have a talk about this ‘friend,’ Sammy.”

“See you soon, Dean.” He turned to Arlene. “I’ve got to go, my brother’s having separation anxiety issues.” 

She kissed him again. “It’s okay. I have a feeling we’ll see each other again.” 

Of course, the whole reason Dean had gotten all fired up to go back to their crap motel so quickly was because their dad had called. His case had led him back to the town they were in, to a planned meet-up with a hunter by the name of Arlene Freeman. On the down side, now he had both his father and Dean watching his every move.

On the plus side, when he could get away, Arlene was more than happy to explore those other positions.


	5. Take It As It Comes

Dean would be the first person to tell you that he was a heterosexual guy. Of course, after losing a spectacular poker bet and giving his first blow job he’d also be the first to tell you that a man’s got to do what a man’s got to do, and that while it may not necessarily be your usual cup of tea it’s not necessarily the end of the world. When he’d taken the ranch hand job he’d fully intended to just work mucking out stalls and such, and that was okay. The money was decent and the work was tiring but predictable, and he was glad to have it. He was doubly glad to have it when Dad’s trip extended again and he was just able to hand over the rent money without a fuss.

But when Ed called him into the house and offered him a hundred bucks for another hummer? Yeah Dean was straight. Yeah Dean was going out tonight to bang Lindsay Sullivan. A hundred bucks was a hundred bucks. It was three boxes of ammo and it was grilled chicken salad for Mr. Fussbudget’s stomach and it was whiskey for Dad and it was whiskey for Dean too if it came right down to it and it was gas for the Impala and it was a start on rent money for next month and it was a decent dinner at a nicer chain restaurant for Lindsay. Damn straight Dean was going to get down on his knees for that hundred bucks.

Maybe another guy would have minded. Maybe the taste would have put him off, but Dean had had ghoul parts literally fly into his mouth. Nothing tasted that bad. And maybe another guy would have objected because sucking cock was something girls did, but well, Dean would have told him that if they wouldn’t do it themselves they sure as hell shouldn’t be asking their girl to do it. Not that he’d be doing it on a regular basis, but hey – if it came to it, there were worse things that could happen.

And they went on and on that way for a good four weeks, with Dad extending his trip and Dean extending his employment, Sam huffing around about their dad like he wouldn’t have been right up and in the guy’s face if he’d have been here. Hell, Sammy’s attitude was probably the real reason he stayed away so much. But then Ed called him in earlier one day, a little before quitting time, and asked Dean to take a seat. 

A pit formed in Dean’s stomach. He was going to be fired. He knew better than to get attached, it wasn’t like he’d thought this thing was permanent or anything, but still the thought hurt. He’d done good work, both on and off the clock. “Is there a problem, Ed?” he asked, looking up.

“Not at all, Dean. I just had a bit of a different proposition for you. You’re free to say no, your employment won’t be affected in any way. And I understand that you might not be interested, I won’t be offended.” Ed smiled gently. 

“What is it?” Dean turned his head a little to the side. 

“I’d like to fuck you, Dean. I’ll give you one thousand dollars to let me be the first one to stick his dick into your tight, virgin hole.” He smiled again, like this was the kind of offer he made all the time. Who knew, maybe it was. “If we both find the arrangement satisfactory and we both want to experience the act again, I’ll give you five hundred every time after that.”

Dean blinked. He looked down, looked up and blinked again. “You want to fuck me.”

“Yes, Dean. I want to pay you to let me fuck you.” 

He bit his lip. Blowing someone for a hundred bucks here and there – that was one thing. Taking money for taking someone’s – well, that was something else. Dean didn’t like guys. He didn’t mind sucking a cock when it came right down to it but this was something else, and he wasn’t sure that this was something he could do. On the other hand, a thousand dollars was a lot of money. A lot of ammo, a lot of Sammy salads, a lot of whiskey, more than a couple months’ rent. Repairs on Baby if she should need them. And, if he played his cards right, the promise of more to come. “All right,” he decided finally. 

“Excellent,” Ed beamed. “You’ll need to shower first – it’s been a long, hot day.” That it had, and he didn’t mind washing up first. He also called Sammy and Lindsay to let them know that he was staying at work unexpectedly and wouldn’t be with either of them tonight. Sam took it better than Lindsay did; the girl was getting too attached anyway. 

When Dean had washed the grime of the ranch off himself he took the robe that Ed had left for him and made his way into the bedroom. He’d been here before a few times, but this was different. This time he was going to be in the bed. This time there was lube on the nightstand, and condoms. 

Lube. And condoms. He gulped.

“Are you nervous, Dean?” Ed stood there, wearing nothing but his jeans and boots. As middle-aged guys went he wasn’t that bad – he kept himself in decent shape, all things considered, and had a better-than-decent six pack on him.

“Maybe a little. This… this really isn’t my thing, you know?” Dean glanced around nervously. 

“It’s okay to be nervous. I’m going to be as gentle as possible and make it as good as I can for you, alright? I’m also not going to expect too much of you.” He pulled at the tie on Dean’s robe. “You have a beautiful body, Dean. Why don’t you take off that robe?”

Dean felt oddly shy but he complied, slowly removing the garment and laying it on the back of a chair. He hated feeling so exposed. “All right. What do you… what do you want me to do now?” He felt his cheeks heat up and knew he was blushing. 

“Relax, Dean.” Ed grinned. “That’s all. I want you to lie down on the bed, on your stomach. That’s all. I’m going to give you a backrub. All right?” 

Dean side-eyed him, but complied. “You’re the expert.” 

The older man laughed. “That I am. Good, Dean. Yeah, just like that. Pillow your head on your arms like that.” He began to rub Dean’s arms and shoulders and just as recommended, Dean did begin to relax. 

This, this wasn’t so bad. Ed’s hands definitely knew what they were doing. He let out an appreciative little hum, almost accidentally. “You have such well-developed musculature, it’s not something I’ve seen before. You must work very hard.” 

“Mmm. Yeah. I work out a lot.” It was the truth, after all. Ed didn’t need to know the types of workouts or why Dean did them. It was enough that he benefitted from them, indirectly when he avoided getting devoured by ghouls or having his heart ripped out by werewolves, and now more directly while he got off looking at the hard body that developed as a result. He let his body relax under the older man’s hands, because Ed was pretty good at this when you got right down to it. Maybe he’d gotten all his money as a masseur. Ed’s hands moved lower and lower, working out every kink and knot in Dean’s back. He took his time even though Dean could feel that he must want to get down to business. He knew, from being on the other side of things, how that felt. Ed didn’t indicate any kind of urgency, though. He just went at his own pace, gentle and unrushed, as he began to massage the globes of Dean’s ass. Dean tensed up for a moment, remembering what else he was going to be doing back there.

He forced himself to relax again. He wanted this. He was okay with it. He wanted this. So when the first finger brushed against his hole, just a whisper of a touch, he used all of his willpower not to clench and resist. “Oh, Dean,” Ed breathed, and reached for the lube. 

Having something – anything – shoved into his asshole was not a sensation for which he had any basis for comparison. It didn’t feel bad. If pressed on it he’d have to say that it felt kind of good although he couldn’t have explained quite why. Ed didn’t have long fingers but the one inside of him felt immense right now, and the stretching sensation was definitely not unpleasant. Ed moved the finger around a bit, letting Dean relax around him and Dean found himself bending his knees a bit, presenting himself to give his partner better access. It just seemed easier all around and Ed seemed to appreciate it, because he grabbed a pillow to prop under Dean to help support him. Dean thought he could get used to this and was just wondering if he could possibly get a girl to do this – maybe at least to try it – when Ed’s probing finger found something buried deep inside him that made Dean howl. His dick, only peripherally involved in proceedings before, suddenly started to take an interest. “What the hell was that?” Dean gasped as his partner dragged a finger across the spot, whatever it was.

“That, Dean, was your prostate,” Ed explained with a dark, wicked smile. “It’s God’s gift to men, and so many men will never know what it feels like.”

“Now that’s a damn shame.” He didn’t even try to hold back a moan as Ed pressed against that bundle of nerves again.

“You like that.” 

Dean barely noticed as a second finger joined the first. “Yeah. Yeah I do.” 

“Good. That’s good, Dean.” Now Dean started to become aware of the second finger, because it wasn’t just hanging around inside as a kind of extension of the first. Ed seemed to be scissoring them, almost, to stretch Dean further. He worked gently, though, so it was only a little bit uncomfortable at first. A little stretchy, a little bit burny, but not painful, and Ed paid attention to Dean’s dick with the other hand which went a long way toward keeping him relaxed. He made sure to keep finding Dean’s prostate, too. That helped. It helped a lot, especially when a third finger got added to the mix. 

Dean found himself enjoying getting fingered open, even though he hadn’t expected that he would. He enjoyed it so much he whimpered when Ed took his hands away, and his partner gave a low chuckle. “I’m just getting naked for you, Dean. Getting ready for the main event.” 

Dean nodded, but he’d have been lying if he said he didn’t feel a bit of fear gripping him. Every dirty little slogan or comment that he’d ever heard for this moment popped into his head. He resolutely pushed them away. “Okay,” he murmured, like he was the soul of patience and he didn’t legitimately need someone or something back there right now. He heard the soft rustle of fabric falling to the floor, the rustle of a condom packet, the squelch of lube. The lube was cool when he felt it drizzled onto his waiting hole, but he forgot about that when he felt the head of Ed’s cock pressing at the rim. This was really happening, and all the prep in the world could not have gotten him ready for this kind of stretch and burn. 

He buried his face in the mattress, not wanting to distress Ed with any kind of expression of pain. It had to feel good at some point, right? Or else people wouldn’t keep doing it? He forced himself to relax with the same Herculean effort it took to keep still when Sammy gave him stitches and waited for Ed to bottom out. He felt his employer stop moving eventually and gave himself a moment to adjust. It didn’t… it didn’t really hurt, exactly. He just felt very, profoundly full in a way that he’d never experienced before. “Okay,” he told Ed. “You can move now.”

Ed took him at his word after a kiss to the neck, pulling back and thrusting in with a motion that Dean had known and practiced for years. Just, you know, from the other side. And Dean had to admit that once he’d gotten used to the sensation of having something else in his body this – well, it felt pretty good, to be honest. The push and pull, the drag and slight burn – he didn’t try to hold back moans of pleasure. Ed had earned them, and he figured the guy was paying for them after all. And all that was when Ed didn’t manage to hit his prostate, which happened regularly enough that the erection that had flagged a bit at the first penetration perked right back up. 

After a while Ed hauled him up, so that Dean was on his knees with his back pressed tight against Ed’s bare chest, wrapped a hand around Dean’s cock and started to jerk. “Come on, Dean,” he grunted into his ear, thrusts not abating in the slightest. “Let me see how you come. I want to see that pretty cock of yours spurting all over the place. Show me how you come. I want to see it, Dean.” He stroked quickly, in rhythm with his thrusts, and Dean couldn’t hold out. He came with a startled shout, spurting thick ropes all over his chest and the sheets. The sight was apparently enough to send Ed over the edge, too, because he lost the rhythm and then stilled only seconds after. They collapsed together into the sticky mess, panting, before Ed carefully pulled out and disposed of the condom.

Dean stayed the night. He figured that Ed had paid for the whole night and should get his money’s worth. Ed paid him the agreed-upon price for another round and Dean went home to Sam tired, sore and reasonably content. 

He went back to work after the weekend with a smile on his face, and when Dad extended his hunt again… and again… and again Dean didn’t worry. He had a very good way of making ends meet.

* 

Sam’s first experience being penetrated came when he was sixteen. He and Tom Wagner had been together for about six weeks, and they’d been a fantastic six weeks from Sam’s point of view. In the year or so since Sam had kissed Amy there had been other people, sure. He’d kissed a few, girls and guys. He’d learned that he loved giving oral, and moreover that he was good at giving oral. But those relationships were fleeting and he’d known it. He hadn’t even felt all that bad when they ended, except for Josh and that was probably just because he was worried about how the guy was going to process his trauma. 

Tom was different. He’d never met a guy like Tom before – no one with the same degree of ambition and determination and brains and sass. No one who had the same weird sense of humor. No one who combined brains and raw athleticism. He couldn’t tell Tom what the Winchesters actually did of course, but he could actually let Tom know what his dad was really like without worrying that he was going to go running to DSS or something. And because Tom knew what Dad was really like Tom could be warned, early on in their relationship, what was going to happen. They were going to move, and it was going to be sudden. Chances were that Sam wouldn’t even get a chance to say goodbye, he’d just disappear one night. 

And Tom, because he knew that there was absolutely nothing that either of them could do about it, accepted it. “We’ll just have to make the most of the time we have together then.” And they did. It was winter, so they went snowshoeing in the state forest. (If Sam brought a handgun loaded with silver bullets and another with consecrated rounds, no one needed to know about it.) They played basketball at the local Y. They studied together, they watched movies together, and because they were both sixteen year old males they made out like bunnies. 

It was great. It was perfect, or at least as close to perfect of a relationship as Sam Winchester was going to be allowed to have. Which was why as the weeks stretched out and they became more comfortable in the relationship Sam’s gloom returned. Tom called him on it one day. “It’s like you’re wearing a shroud instead of a hoodie,” the local pointed out. “Who pissed in your cereal?”

Sam snorted. “It’s just… I’ve been here for all of three months, right?” 

“Yeah. It’s been great. Well, the last six weeks have.” 

“I’ve never stayed anywhere for three months. Not since I was six months old. I’m going to have to leave soon and I hate that. I hate that I’ll have to leave and I hate the not knowing. Whatever… job it is that my dad and brother are on can’t last much longer.” 

Tom kissed him, slow and deep. “I thought we agreed that we were going to enjoy the time we had together, Sam.”

“I do. I love the time we spend together, I love how you challenge me in class and I love how you make me feel all safe and stable outside of class and I love how you do that thing with your tongue right at the base of my –“ Sam broke off as Tom nipped at his neck, laughing weakly. “Seriously, though. I just… I’m not ready for it to end, you know?”

“I know,” Tom admitted. He sighed, and then he smiled at Sam again. “I know, and I’m with you. But as long as we’re both minors there’s not a lot we can do about it except deal. So – let’s deal.” He kissed Sam again, licking into his mouth insistently, and Sam let him. 

It didn’t take long for them to both wind up naked. Tom’s parents were gone for the weekend – some kind of cheerleading competition his sister was doing – so they were at his house, with no worries about anyone finding them, and frankly both of them liked to be naked around each other. They liked looking at each other, and they liked the other looking at them. It was a nice way to be, uncovered as though you didn’t have anything to hide or be ashamed of. And it wasn’t as though either of them could keep his hands off the other as a general rule. Tonight they grappled a bit, as sometimes happened, although Sam usually let Tom get the upper hand. He had to admit that while he enjoyed giving oral he also loved it when Tom slipped a finger or two inside of him, brushing against his prostate and leaving him whimpering. They’d messed around a little bit like that, not really progressing much further. He knew that Tom had a little bit more experience than he did just because he’d been in one place longer, had more opportunity, but they hadn’t been rushing things. 

Tonight he let Tom get him on his back and slip a dry finger into him, not holding back a moan since there was no one to hear that he didn’t want to hear him. Tom grinned and bit down on Sam’s collarbone. “Yeah, you like that, don’t you?” 

“You know I do.” He let his knees fall open to offer better access. He groaned as his boyfriend grazed his prostate when he added a second finger. “I love having your fingers up in me.” 

“I know it.” He raised himself up a little, put a pillow under the small of Sam’s back to give him a better angle. “You ever think about…” 

“What, sex? All the time.” 

“I mean with each other.” He brushed Sam’s prostate again, tickled the base of Sam’s cock with his tongue. 

“I’m lying on my back with your fingers in my ass, your tongue on my dick and you think I don’t think about having sex with you?” Sam raised an eyebrow. “Seriously?” 

“You’ve never had sex before. Not full-on, penetrative sex.” Tom bit his lip. “I want it to be special for you.”

“Tom – you are special. That’s what makes it special for me, okay? You. Not some date on a calendar, not some slightly-less-seedy motel, not a school dance or something. You.” He tried to focus on the sensation of Tom’s fingers inside of him. “You’re what I care about. If you want it, I can’t think of anyone else I’d rather it be.”

The other boy leaned in and kissed him again. “Are you sure?” 

“I’m absolutely sure.” He smiled up at Tom. “We might not have forever, or even the rest of the school year. But we’ll have this, right?” 

Tom chuckled. “Right.” He reached over into his nightstand and pulled out a bottle of lube. “Let’s do this right, then.” 

Sam already had two fingers in, but Tom wanted to be sure that Sam wasn’t going to be hurt so he took his time stretching Sam out. He used plenty of lube when he added the third finger, working Sam open patiently and diligently like he had some kind of a timer in his head. Finally whatever schedule he’d been working to was met and he slicked himself up and lined himself up with Sam’s hole. “You’re positive you’re okay?” Tom verified.

“Please,” Sam whimpered. “Please, just… I need you.” He hooked his legs over Tom’s hips. 

Tom’s initial entry was not comfortable. He’d taken his time and prepped him right but a cock was different from fingers and there was no getting around it. Tom pushed in slowly and let Sam’s insides adjust to the intrusion so it was only a slight stretch and burn instead of pain. He waited for a moment and let his body tell him when he was ready. “Move, please,” he whispered to Tom. 

Tom accommodated, pulling his hips back and snapping them forward. Sam threw his head back and moaned. He knew he wasn’t going to heaven, but if he were it would feel like this. Tom’s face showed that he was probably thinking along the same lines, amber eyes glued to Sam’s face as he thrust back and forth. “Sam,” he gasped. “You feel amazing.” 

“Tom,” he groaned. “Don’t stop. Whatever you’re doing, do not stop.”

Tom obliged, bringing a hand in between them to jerk Sam off in perfect rhythm with his thrusts. It was too much – Sam came with a cry that you could probably hear on the moon, painting both of their chests with his release. Tom followed moments after, collapsing against Sam and not caring what a mess they made.

Sam, the urge welling up in him from some deep and unexpected place, licked Tom clean. Tom’s body, which had seemed spent, perked right back up again. Sam would have been lying if he said that the thought of another round didn’t excite him, so he rolled over and let Tom take him from behind this time. He was sore, but it was more like the soreness that comes after a decent workout than real pain. He wanted more. 

After round two they decided to take a shower. Of course they’d decided to shower together, which meant that once they’d washed themselves up Sam found himself so grateful for what Tom had just given him that he decided to blow him in the shower and Tom just had to return the favor, but the Wagners had an in-line hot water heater so that was okay.

When they got out of the shower, shivering and damp and sated, they returned to Tom’s room to find Sam’s cell phone ringing. It hadn’t rung once during the entire time Dad and Dean had been on their hunt. Now his father was calling. With shaking hands Sam pressed the green button and held the phone up to his ear while Tom held his breath. “Is Dean okay?” Sam asked before his father could say anything. “Is Dean hurt?” If they were still on the road his father would never call Sam if Dean were capable of calling.

“Dean is fine. We’re at the motel. Where the hell are you? You’re not in your position, Sam.” 

Sam tried very hard not to think about the position he’d been in most recently. “I’m at a friend’s house. We were studying.”

“Did you have permission to go to this ‘friend’s’ house?” 

Sam sighed. “No, sir.”

“Get your ass back to the motel. We’ll deal with this in person.” The line went dead in his hands.

Sam turned to Tom. “That was your dad, huh?” His boyfriend’s face had gone pale.

“Yeah. Tom –“

“He’s not happy, is he?” 

“Yeah, well, he got back to the motel and I wasn’t there so no. He’s not.” 

The other boy blinked a few times. After a second, Sam realized he was blinking back tears. “It’s not like you even knew he was coming back today, right?” 

Sam snorted. “I haven’t heard from him in three months.” He felt the tears in his own eyes, but fear held them back. “No, I didn’t know. I’m sorry, Tom.”

“I’m not.” He kissed Sam for the last time, deep and passionate. “We knew this was coming eventually. I’m glad he couldn’t take this away from us, Sam.”

“I love you, Tom.”

“I love you too.” 

Tom gave him a ride back to the motel, although they agreed for everyone’s safety that he would drop him off at the edge of the drive instead of coming up to the door and meeting the family. He was out to his family, but he got that for some folks the closet is a nice and warm safe space. 

Dad was livid that Sam hadn’t been in the motel room on a Saturday evening, waiting for him and Dean to get back, but even he had to admit that he had given no warning and he couldn’t find any other fault with Sam’s performance while he was away. Sam was even all packed up and ready to go, never having unpacked in the first place. They were out the door and en route to Maryland that same night.

Sam rode with Dean in the Impala. Dean talked at him about the hunt they’d been on, but Sam mostly tuned him out. “Jesus, Sam, no wonder Dad gets so pissed at your attitude if you can’t show a little bit of interest in a three-month hunt,” he snapped after Sam continued to stare out the window and respond in grunts or monosyllables. “You’d better get your priorities straight. It’s not like you had anything going on to mope about.”


	6. Anything Goes

Dean’s liaison with Rhonda Hurley happened when he was nineteen and living in Florida. Dad was off chasing yet another Very Important Lead and Dean was left alone with Sam yet again – morose, hormonal Sam who was in another of his “I’m not talking to anyone about anything and if you touch me I’ll stab you in your face” kinds of phases, and that wasn’t hyperbole either. After the whole thing with the gladiator cult – and wasn’t that a shit show and a half – the kid had just shut down and when Dean had tried to comfort him after a nightmare he had almost lost an eyeball. Sure the kid was traumatized, but he needed to get over it. They were hunters. These things happened. 

Well, maybe not the loincloth.

But the point was that he’d survived, and that meant he needed to suck it up and deal and move on to the next big bad. Not get all surly and stabby and blaming Dad for it, like it was Dad’s fault that the trap hadn’t gone according to plan or something. They were hunters. Sometimes things didn’t work out. The point was that they saved lives – that Sam had saved lives, killing all those cultists. And he needed to quit with all of that “this life is killing us and I’m not willing to do it” crap. So Dean got sick of listening to his brother whine and cry and try to weasel out of doing his damn job and found something better to do with his time, and that something was Rhonda Hurley. 

She was everything that a guy like Dean was looking for at that time. She was curvy. She was all smiles in comparison to Sam’s constant scowl, and she was adventurous. She didn’t care about commitment, she didn’t care about monogamy. She lived in the now, a lot like Dean himself, and she didn’t regret it for a moment. He got a job at a scrap yard – not great work, but it was a job and it kept food on the table while Dad went off and did his thing. His days mostly consisted of work, training, sex and trying to avoid Sammy as much as possible. He felt kind of bad about that, but if the kid weren’t being such a little bitch about things maybe he’d stick around more. 

One day he got a call from Rhonda while he was on break at work. “So listen,” the brunette told him. “Are you busy tonight?” 

“Not if you’ve got something you want me for, sweetheart.” As it happened his father had told him to take Sam out and work on night shooting, but it wasn’t going to take much to dissuade him from that course of action. He usually wasn’t a big one for disobeying orders but these days when it came to a decision between time with Sam and his dick… 

“Well, I’ve got this guy. And he’s… well, he likes to watch. And he’s willing to pay… to watch. And I got to thinking, who do I know who wouldn’t mind showing off a little, huh?” 

He hesitated, feeling the blush spread over his cheeks and highlighting every freckle. “Yeah. Uh, I don’t know, Rhonda. I’ve never exactly put on a show for anyone before, you know?” 

“Really?” she squeaked. “I find that hard to believe. You’ve put on a show for me every time you’ve fucked me, Dean. I know you can do it for me again. Just forget about the other guy watching – I know it’s not the money thing that bugs you. I mean, I’ll split it with you fifty-fifty.” 

He nodded in acknowledgement – she knew about Ed, after all. It wasn’t like he was ashamed. “It’s important to you?”

“It’s good money, and I like the idea of someone watching you slip your dick inside me Dean.” She gave a low, dirty laugh. “I want someone to have to sit there and watch you come all over me.” 

“All righty then. I’m in.” Maybe he could get Sam to do his own night shooting. 

The rest of the day went quickly after that. He called Sammy and passed along his revised version of Dad’s instructions, hung up on the objections (“I have exams,” “It’s illegal,” “What the hell kind of stupid crap is that, wanting a fifteen-year-old to go shooting in the dark by himself, someone’s going to get killed or worse!”) and drove over to Rhonda’s.

She was waiting for him at the door of her trailer wearing a tight tank dress that left nothing to the imagination. “All right, pretty boy,” she ordered. “Shower.” 

He obeyed – the scrapyard was dirty work, after all – and made his way to the trailer’s one bedroom. There he found her waiting with an array of… “Satin panties?” he questioned, raising an eyebrow. 

“Mmm-hmm. Bob is a kinky guy. He’s already agreed to a price but he might tip us a little extra if there’s a little bit more of a show.” She swatted him once on the ass for emphasis, hard. He yipped, but he couldn’t hide the fact that his dick twitched. “Very good.” She reached out and chose a pair of hot pink panties for him. “Try these on.”

“I don’t know, babe. This seems…”

“Just do it, Dean. Trust me.” 

He considered resisting. He really did. At the end of the day, though, it was just panties. Really, just a scrap of cloth. And someone was going to pay him for it – well, for things involving it. But really, what did it matter about a pair of panties? He’d done things that should threaten his masculinity far more than a little bit of satin and come through with his heterosexuality very much intact, thank you. He took the underthings and stepped into them, pulling them up and facing Rhonda. “Nice,” she told him after looking him up and down. “Very nice. I think you think so too.”

He had to admit that he did. The color was a good one for him, and the feel of the satin around his cock was – well, it was exciting. He was getting a little hard just from that slippery, silky sensation alone. When he pulled up his jeans and let the hard zipper rub against his threatening hard-on it was even more pronounced. Oh God. He was in trouble. 

The drive to the hotel was quick, and Rhonda filled it with instructions that Dean only half heard. He was supposed to let her direct the staging and everything even though Bob liked the woman to appear more submissive, because he’d never performed for an audience before. Yeah, he could do that, focus on her, pay attention to her cues, blah blah blah, but did she know about how the panties had shifted and were riding up his ass right now? And how that was probably not supposed to be a good thing, but it was really creating a problem for his dick? 

Rhonda knew exactly where in the hotel they were going, so he just followed along and debated the wisdom of adjusting the panties. Bob, an older man in nice clothes, sat in a chair on one side of the room from the bed. He handed Rhonda an envelope, which she glanced cursorily into before caressing his face with her hand and introducing “Dan.” “Dan knows what we’re here for, don’t you, Baby?”

“Why don’t you show me, then?” Bob urged, already sweating. Dean could sympathize. Rhonda’s dress could do that to a lot of guys. 

Dean took off his shirts. Rhonda pressed up against Dean with her back, presenting her front to the client. He guessed he was supposed to touch her like this because it gave Bob a clear view so he obliged, nibbling her neck as he let his hands roam along the outside of her garment. He left his hands gentle at first, moving slowly and taking note of the absolute lack of undergarments before starting to tease her nipples in earnest. She moaned maybe a little louder than she normally would at this stage of the game, probably for the client’s sake. That was okay. Dean could see that it wasn’t all show; her nipples hardened into stiff peaks under the spandex dress. He petted her crotch outside her dress and she groaned, angling her hips to make sure he could get an angle to touch something worth the effort. He didn’t stay outside the dress for long. “You ready?” he whispered into her ear. She nodded, imperceptible to anyone who didn’t have that magnificent head of curls pillowed up against his shoulder, and Dean grabbed the edge of that short dress and pulled it up and off.

He snaked his hand back around and began to worry her clit with his thumb, plunging a finger into her as she rocked and moaned. Dean let his eyes travel over to Bob. Bob’s eyes were glued to Rhonda, but they couldn’t settle on just one place. He stared at her face, her breasts, her groin and he bit his lip. “Yes,” the client hissed. “Touch her, just like that.”

Dean grinned. He had to admit that Bob’s voice, his praise, was having an effect on him. He rubbed his own crotch against Rhonda’s ass, looking for some friction. Between the panties and the heat of Rhonda’s body he definitely got what he was looking for as he ground against her. She turned around slowly, keeping her body angled so that Bob could see most of her and what she was doing to Dean as she reached out and unbuttoned Dean’s jeans. Then she pulled them down, sinking slowly to her knees as she did so. 

Bob let out a slow groan as Dean stepped out of the jeans. “Do it,” Bob told her. “Put your mouth on him.” Rhonda winked up at him and obeyed, mouthing Dean’s hard-on through the panties. He tossed his head back and moaned, low and deep. The panties were one thing, hard to resist. Her mouth was also a gift from God to the world. The combination was too much. He gripped himself at the base after a minute, grabbing her hair gently but firmly to hold her still. Bob wouldn’t want to end the show so quickly, would he? 

She winked up at him before turning to Bob, still on her knees. “How do you want me, Bob?” 

Bob swallowed hard. “On the bed,” he decided. “O-on your belly.”

“I can do that.” She went over to the bed and bent over it, feet on the floor and legs spread wide for Dean. Dean dropped to his knees. “Don’t move, sweetheart,” he told her, before licking a long stripe up from her clit to her ass. She let out a surprised – and enthusiastic – moan. Bob’s groan was even louder. He moved his tongue back down to work the clit, feeling his body calm as he focused on making her scream into the mattress. Finally Bob could take no more. “Now, Dan!” he demanded. “Do her now!”

Dean didn’t need to be told twice. He pushed the fabric of the panties down to free his dick, grabbed a condom, rolled it onto himself and plunged into Rhonda’s wet heat. All three of them cried out in unison when he entered her. 

He came harder than he’d ever come before. He didn’t know if it was because of the panties, or if it was because of some particular trick Rhonda pulled that night, or because he just needed the release after listening to Sam bitch. If he had to think about it though he’d have to guess that it probably had a lot more to do with the fact that Bob was watching and cheering them on. 

After they left they went back to Rhonda’s trailer and split up the money. Bob had indeed given them an extra tip – four hundred dollars on top of the thousand he’d given them for the initial payment. That meant seven hundred dollars Dean hadn’t planned to have, all for having mind-blowing sex with someone he’d planned to screw anyway.

When he went back to the Winchesters’ rented trailer he found Sam sulking in a corner doing homework. He wouldn’t say a word to Dean, but he had three targets with perfect grouping. At least Dean could justify the alteration in his father’s orders. Sam hadn’t needed him to get his shooting done, and he’d managed to make the family some extra money. The fact that he’d gotten off and avoided his brother’s teen angst didn’t even need to enter into the picture. 

*

Sam blinked at Brady. “You want to what?”

“I want to spend the night with Bill and Derek,” his boyfriend repeated. “I used small words, Sam. It’s not hard to understand.” 

“You want to go sleep with Bill and Derek.” Sam folded his lips together and nodded his head. He’d known it was too good to be true with Brady. His father was right: the idea that anyone would actually want him had been too good to be true. Brady had gotten bored with him, or finally all the scars had turned him off, or maybe it was shame. Maybe he was just ashamed of the fact that his boyfriend couldn’t afford a wardrobe he could be seen in public with and didn’t have a family and –

“I can see the wheels spinning in there, Sam.” Brady put an arm around him. “Stop. I mean, yeah. Bill and Derek are hot and yes, I want to sleep with them. I want us to sleep with them, Sam. Together. All four of us. They’ve invited the pair of us – as a couple – to come over for a kinky little sleepover and I told them I’d run it by you.” 

He forced himself to calm down. “A ‘kinky little sleepover?’ What exactly does that involve?” 

“I have no idea. I mean, I don’t think they’re into anything too heavily BDSM or anything. We’ll talk over the ground rules and everything. I think it could be fun, maybe a little bit different. It’s college, time for experimenting. It’s your birthday, Sam, or it was a day or two ago. If you’re not up for it, that’s fine. I just figured it would be a good way to blow off a little bit of steam after finals and with your birthday and all that - you seemed so down.” The blond gave him a gentle, loving smile.

He sighed. “Yeah. Yeah, I’d like that.” Truth be told he was still a little edgy about the whole thing, but it would be fine. It had to be fine. He hadn’t found the restraints he couldn’t get out of yet. Well, he could get out of them eventually. And people did group sex things all the time, right? It didn’t necessarily mean killer gladiator cult. “No clowns?” 

“No clowns. I checked.” He kissed Sam gently on the lips. “It will be fun. I promise.” 

Sam would have preferred a quiet night of bad television with Brady and maybe Luis, but well, Brady deserved to blow off a little steam, too. Freshman year had been a challenge for both of them. Brady had always been a little more adventurous than Sam, and if this was what he needed to feel like he was putting the negativity of the year behind him, then so be it. “Okay. Yeah, sure. I’m in.”

Bill and Derek lived in an apartment near campus, close enough to walk, so walk Sam and Brady did. Their hosts met them with big smiles, and Sam started to relax. It wasn’t like these guys were strangers. Brady knew them better, but Sam knew them both, too, Derek from his mock trial team and Bill from soccer. He’d had no idea they knew each other, never mind that they were together, but they seemed to have a level of ease with each other that suggested their relationship was of some duration. They shared some wine and established some ground rules, a safeword (bacon, suggested by Derek) and glanced at each other. 

“What happens now?” Sam asked, licking his lips nervously.

“I’d like to blindfold you, Sam, if that’s okay,” Bill suggested. Bill had this really smooth voice, very calming. He could be a hypnotist; instead he was a theology major. “If we could take off your shirt first so the blindfold doesn’t get disturbed later that would probably be best.” 

Sam thought about saying no. He could do that – why should he be the one blindfolded, after all? But that wouldn’t be showing trust. And he wanted to show Brady how much he trusted and loved him. He removed his shirt. “Let’s do it.”

He closed his eyes and let someone tie something over them. “The thing is, Sam, you worry too much,” Brady murmured into his ear. “You need to lighten up. Loosen up. Have a little fun without worrying about what’s going to happen. So what you’re going to do is sit back and enjoy yourself, alright? You’re going to let three very hot men take care of you and of each other. And you’re going to like it. Got it?” 

Sam laughed. If only ‘lightening up’ was that easy. “I can try,” he promised, and he grabbed his boyfriend and drew him in for a kiss. Hands wrapped around him from behind and someone began to nibble on his neck even as he licked into Brady’s mouth. He couldn’t help but relax into the embrace, especially not once someone started touching his nipples. He shouldn’t let his guard down - anything could happen. His body was not cooperating with his need to maintain vigilance, however.

“Maybe we should move this party into the bedroom?” suggested Bill from a couple of feet away – it was Derek who had grabbed him, then. 

Brady broke away from him and took him by the hand, and the quartet moved single file toward the bedroom. 

It was hardly Sam’s first time moving blindfolded; it was probably the most fun, though. He could relax; these were good people. If he repeated the sentence often enough in his head maybe he could make himself believe it.

Once in the bedroom Brady cleared his throat. “Sam, I’d like to tie your hands up. Is that okay?” 

“What? Why?” he demanded quickly, hands disappearing behind his back without the interference of his brain. 

A pair of hot calloused hands, slightly smaller than his, caught them up and began to to suck on the fingertips of the left. “Because, Sam,” his boyfriend explained. “You’re not… you’re not relaxing. I know you. You’re still tense. You’re still rigid. The whole point of this to have you accepting love and attention. You sitting back and accepting love and attention the way you were clearly intended to be adored. This way,” he continued, running something smooth and silken along Sam’s bare torso, “you have to accept our adoration. You can’t hide. You just have to bask.”

He considered, unable to keep from shaking his head at the idea of basking in love like some kind of lizard on a rock. He didn’t think that they’d be able to bind him in a way he couldn’t escape. And he was supposed to be showing his trust, and learning to relax and be taken care of. Right? “Sure, Brady. Whatever you want.” He held them out in front of him. 

Someone started kissing his neck again, almost sucking where the neck met the shoulder and he gave a little groan. He’d always liked it when people paid attention to his neck. But now someone else was mouthing at his nipple as a third someone started binding his hands and forearms together with some kind of silk belt – maybe from a bathrobe? “Oh – that feels nice,” he admitted. Maybe this wasn’t such a bad thing. He could always get free if he needed to. He knew these guys, it wasn’t like they were strangers, and he loved Brady. Was there really any harm to letting go for a little while and letting himself enjoy the attention? It felt good, at least. Did he have to question it? 

Once his hands were bound, lips connected with his and he was guided over to the bed. He leaned back into the chest of whoever was nibbling on his neck – had to be Derek again, if the goatee was anything to go by – and felt hands petting him. Not all of the hands were on him, of course. The others were getting naked too, and only after he’d heard the rustle of all of their clothing did he feel anyone tugging at his own garments. He waited patiently – he was good at waiting until the time came to strike – for the person taking off his lower garments to stand up again before circling his legs around their knees and pulling, so that they fell forward on top of him. Bill chuckled. “Looks like someone needs a little attention.” He kissed Sam, licking into his mouth. “I’m glad to see you’re getting into this, Sam.” 

“Sam likes kisses,” Brady said from somewhere nearby. “I knew he’d get into this eventually, once he loosened up a little.” 

“Oh, I think he’s going to need a little more loosening up than a few kisses,” Derek rumbled, running a hand along Sam’s flank. “What do you think about that, Sam?” 

“I think you’d better start loosening me up then, Derek,” he retorted, breaking the kiss. The sophomore laughed and moved away from behind Sam. He was still propped up on someone’s chest but that someone was thinner and smaller. He was pretty sure that he recognized the erection pressing into his back as belonging to Brady, but he didn’t pause to think about it as Derek’s wide mouth closed around the tip of his cock and moved slowly down. 

Someone somewhere produced lube and two slick fingers slid into Sam. He gasped at the intrusion and the way Derek slowly moved his mouth down the shaft of Sam’s cock. “Oh, fuck!” 

“Nice, isn’t it? The things he can do with that mouth – well, I’d say you wouldn’t believe it but you’ll both figure it out soon enough.” Bill’s voice came from somewhere near the nightstand. Sam realized that Brady’s arm was moving. “It’s incredible. And those thick fingers of his – can’t ask for better prep than that, can you, Sam?” 

Sam gave into the sensation because Derek really was very, very good at what he did. When he was good and stretched, though, it wasn’t Derek who mounted him. He found himself helped into a prone position while someone else – probably Brady, he recognized after a moment – lined up at his back. Someone else placed something gently at his lips. A thrust of his tongue told him that it was another cock – not that he was even remotely surprised, all things considered – and he opened his mouth and took it in even as Brady thrust into his ass. “Hang on,” Derek grunted from somewhere a little farther away – probably behind Bill. Both Bill and Derek let out huge groans, and the group developed a rhythm. 

Sam had never felt so full in his entire life. He should feel humiliated. He should feel disgusted. Instead, he felt beautiful. He felt alive. Maybe it had been frivolous, but he’d done something entirely for pleasure and it had been unrushed and with no pressure. No one had died, he hadn’t let anyone down by taking a few hours to indulge himself and his lover. He and Brady went back to the apartment they’d rented for the coming year after breakfast the next morning, everyone satisfied and everyone content.

Sam was happy.


	7. You and Me and the Bottle Makes Three

The table in the motel of the week was unstable but that was okay. It didn’t need to be terribly stable to hold up his laptop, and he could prop it up with some cardboard anyway. It probably counted as a metaphor for himself or something. Sam Winchester, hunter and metaphorical table. As long as he got the research done no one really gave a crap how unstable he got. Hell, it wasn’t until he’d gotten away from Dean and wound up in the hospital that anyone would admit that the hallucinations were a problem, and that “anyone” had included Sam himself so maybe the unstable table analogy was more spot-on than he’d thought.

Or maybe he should call it quits on the research for the night and get some sleep. 

He glared at the screen. He couldn’t just leave it, of course. It was pretty much his only purpose here anymore. He didn’t talk much anymore either, not even to Dean. He wasn’t much use in the field, everyone had made that abundantly clear, but he wasn’t allowed to just die peacefully. He had very few contacts, no more hobbies. This was the only reason he was here - well, that and so Dean had someone to talk at. 

The key turned in the lock, and he tensed. Dean had gone out to a bar. Either he’d struck out, in which case he’d be drunk and cranky, or he’d have company. Either way, Sam needed to shut down his laptop and be ready to react. When Dean walked in it took all of about three seconds to figure out that he wasn’t alone. The woman beside him was taller than Dean’s usual type, with dark hair and skin. “Heya, Sam,” he greeted, the scar on his arm standing out angry and red. “I need the room.”

Sam sighed and grabbed his duffel, putting his laptop into its case. This might have been okay years ago, when they were younger and Dean was going to Hell in a few months. Now it had lost most of its charm. Somehow it didn’t seem quite right that Sam still had to spend nights in the Impala when he wasn’t the one favored enough to get a nicely rebuilt body after Hell. He stalked toward the exit, ignoring Dean’s completely unapologetic smirk, when his brother’s date interrupted. 

“Oh, Dean, come on. We don’t need to be making your brother sleep out in the cold like that.” She strutted right up to Sam, who had frozen in place. “You’re a tall drink of water, aren’t you?” 

He folded his lips together and forced a polite smile. “Yeah. Yeah, I’m tall.” 

Dean rolled his eyes. “Gwen, Sammy doesn’t mind sleeping in the car and giving us a little privacy. Do you, little brother?”

Gwen’s lips curled slowly. “Brothers. Very nice. I think I’d like for your brother to stay, Dean.” She darted a glance at her original date before looking back up at Sam and reaching out to touch his chest. “You don’t mind, Dean.”

Dean grimaced. “Gwen, baby, I don’t mind a threesome, but I’m pretty sure Sammy isn’t that kind of guy. He’s more like a monk, really. Hasn’t even talked to a woman in what is it, two years? Sammy, car. Now.”

It had been a long time for Sam. He wondered how badly Dean had pissed Gwen off that she was pretending to be interested in him. Still, she was playing it off well, and it was annoying the brother who thought the Impala was a good place to stash a younger brother for the night, and even if it was fake it had been so long since someone had even looked at him twice that he was going wallow in it for a little while. He tossed a quick smirk at Dean before running a hand through Gwen’s glossy hair. “How did you meet Dean again?”

“In a bar. You know how it goes.” She looked up at him through lashes that looked entirely natural. “Your lips are very nice Sam. Do you know how to use them?” 

Dean made a strangled sound as Sam inclined his head toward Gwen’s lips, cupping her face with his hands. Her lips might have been a little on the thin side but they surrounded a generous mouth and she knew how to use it to entice, to warm. She wrapped her hands in his hair and tugged, just a little bit. 

Dean cleared his throat. “You can feel free to join in anytime,” Gwen called to him. “There’s plenty of me to go around, you know. You don’t have to touch your brother if you don’t want to.” She winked up at Sam, who drew her back in for a kiss. 

Of course there wasn’t going to be anything like that. Hell, he still had his doubts about an actual threesome taking place. Gwen was probably just trying to rile Dean up. Except here was Dean, storming over with his face looking like a thundercloud until he got his hands onto Gwen’s hips. He started nibbling on the woman’s neck and she let out an appreciative moan. Sam stepped back. Things were back to the way they should have been, Dean got the girl and at least Sam had gotten a kiss or two out of the deal. He moved back to his duffel and his laptop bag, scooping up the keys to the Impala while he was at it. 

“Where do you think you’re going?” the lady snapped, lifting her head up from Dean’s shoulder. “I thought you understood. Three-way or no way.”

Dean made a face. “You heard the lady, Sam.” 

He met his brother’s eye. “You seriously okay with this?”

“Me? I’m fine,” Dean told him tightly, wrapping his arms around Gwen. “It’s you I’m worried about. Threesome is kind of kinky for you, Sammy.” 

“It’s really, really not, Dean.” He shifted his gaze down to Gwen. “What about you? Are you sure about this?”

“Oh hell yes. One of you was pretty enough but when I saw that there were two of you?” She grinned and walked over to the bed, leading Dean by one finger. “There was no way I was going to pass up the opportunity.” 

Sam gripped at the scar on his hand, but everything stayed the same. The scenario was real, then. He quickly shucked off his flannel shirt and sat beside Gwen on the bed. 

Her eyes widened. “Those arms,” she marveled, running a hand over his bicep.

“He does yoga,” Dean told her, moving around behind her to rub at her shoulders.

“You should try it sometime,” Sam suggested, before moving his mouth back over to Gwen’s. 

“How about if I give you a nice big bucket of ‘no’ there Sammy?” Dean slid his hands up underneath Gwen’s sweater. “There we go.” He eased the garment up and over her head, dislodging their kiss. 

Working with Dean on foreplay was kind of like choreographing a fight. It had been a long time since the Winchester brothers had been in sync on much of anything and for a lot of reasons, but when it came right down to it if you put them into a fight they worked like they’d never been apart. Dean went ahead and lavished attention on her round nipples, finding that she much preferred a little suction and his nimble tongue to anything he could do with hands. Sam, by contrast, stuck with his strengths and focused his mouth on the space between her legs. He liked it, she seemed to be enjoying it, and her cries definitely seemed to make Dean’s jeans fit a bit differently. 

Sam could probably have satisfied himself with tasting Gwen all night, or come close to it anyway, but after her third prayer (or was it blasphemy?) of the encounter she demanded a break. Dean immediately shucked off his jeans, and of course he’d gone commando tonight. Sam averted his eyes out of politeness, instead holding Gwen’s hair and patting her back as she took Dean deep into her throat in one smooth motion. Huh, he thought. Gwen might like sucking cock as much as Sam did. She looked perfectly content as she hollowed out her cheeks around Dean’s shaft, playing with his balls and toying with the space just behind them. She definitely knew what she was doing, too. Dean threw his head back and moaned like a porn star until his breathing grew ragged and he finally came with a half-agonized cry. She swallowed everything she could, using a tissue to mop up what had spilled out the side.

Sam pulled her back into his arms against his chest, giving her a comfortable place to rest and catch her breath. Even though he wasn’t exactly looking he could see that his brother wasn’t exactly small. “You did great,” he murmured into her ear, petting her hair. “You were fantastic.” 

She met his eyes and smiled. “You ain’t seen nothing yet, baby.” She unzipped his jeans slowly, pulling them down and enlisting Dean’s grumbling help in removing them. She peeled back his briefs to release his cock and stared. He felt his cheeks pinken. 

“Jesus, Sammy,” Dean groused, looking away. “You’re gonna poke someone in the eye with that thing.”

Sam glowered. You just didn’t comment on another guy’s parts in a threesome, not if you weren’t going to do something with them, and neither brother was up for that. At the same time, Sam didn’t want to think about Dean or etiquette right now.

Gwen, on the other hand, reached out. “Dean, pass me a condom.” 

His brother gave a wicked grin before getting a condom from the nightstand. “Think you can take him, sweetheart?”

“Probably.” She winked at Sam, who snorted and rolled his eyes. Sure he was big, but he wasn’t that big. She rolled the condom onto him and then she lay on her side with her head in Dean’s lap. Sam lined himself up and she wrapped one leg around his knees, propping one ankle on his shoulder. He sank himself slowly into her wet heat, prompting a cry from her. He paused, but it turned out to be a cry of pleasure. He set a moderate rhythm - this angle was challenging and he didn’t want to finish too quickly, especially not considering how long it had been for him. Her cries let him know that it was working for her too, although when Dean snuck a hand in to work her clit as Sam slammed home she screamed and clenched around him and that was all he needed. He disengaged carefully, disposed of the condom on shaky legs and collapsed back into the bed. 

They treated Gwen to breakfast the next morning and returned to the motel after dropping her off at home. Sam expected Dean to focus on the case, never speaking of the night before again. He found himself surprised when his brother turned to him as soon as the door was closed behind them. 

“Dude,” he complained. “What the hell do you mean that wasn’t your first threesome?” 

Sam blinked. “Seriously? Do you really think I’ve been a cloistered monk all these years, Dean?” He shook his head and went to go boot up the laptop.

“All right then. When was your first threesome?” 

“It was a foursome and it was freshman year.” One of the four was dead - Sam had killed him while killing the demon possessing him. Sam himself had died… oh, maybe six times now? He was kind of afraid to look up Bill or Derek. “You?” 

Dean blushed. “Doublemint twins. Not long after the first time you died.” He shook his head. “That just sounds wrong. Do you even remember all your firsts?” He sat down on the edge of the bed.

“Sure. Why?” 

“First kiss.” 

“Dean -”

“First kiss, Sammy!”

“Amy Pond.”

“Oh.” He looked away. “Um. Mine was Robin. From New York.” 

Sam shifted. “She seemed nice.” 

“She was. Beautiful girl.” His face fell for a moment, but he picked it back up. “First blowjob, Sammy?” 

“Dean, we are not playing this game.” 

“I want to know!”

“No, Dean.”

“I’ll tell you mine. It was in the concession stand - hey, you remember that school in West Virginia, the one with all the grades in one building?”

“Aw, man! I bought a root beer there!” 

“At least it wasn’t a cream soda, Sammy.” 

Sam wanted Dean to stop, he really did. He gave some thought to taking the laptop over to the public library to enforce his desire for Dean’s live-action Penthouse Forum session to stop. Before he could pack up the machine, though, he noticed something. The brothers hadn’t spoken this much to each other about something not directly related to a case since before the Apocalypse. No one was shouting at one another No one was walking away. No one was throwing anything. 

“Come on, Sammy. Quid pro quo,” Dean insisted. 

“What are you, Hannibal Lecter?” He glared. “Fine. Tom Wagner, junior year back in Wisconsin. Happy?”

Dean’s eyes bulged. “Seriously? First person to give you head was a dude?” 

He’d never formally come out to his brother. He never figured he needed to, but the look on Dean’s face right now was priceless. “Yup.”

Dean’s green eyes grew calculating. “Wait a minute. That was when Dad and I were on that three-month hunt and you were such a sulky little bitch in the car.” 

“Yeah, well, first time I had sex and then you guys show back up that same day yeah I was pissed, Dean.” He tried to keep his face nonchalant, but he could feel the corners of his mouth twitching as he tried to contain his laughter. 

“Wait - the first time you fucked someone and you didn’t even tell me?” Dean sputtered. 

“Nope.” 

Dean processed that for a moment. Sam could practically watch the discs spinning in his brother’s head. “You… let… some guy…” 

“Yahtzee.”

“Did he pay you?” 

“What the hell, Dean? No, he didn’t pay me. He was my boyfriend.” He threw a paperclip at his brother.

“Hey, don’t go judging. It’s not a bad way to make a few extra bucks if you can be safe about it. But - wait. You like girls.”

“There’s a word. Bisexual. Say it with me.” He contemplated what his brother had just admitted to doing. “You’ve gotten paid for sex?” 

“Yeah, I have. And there’s nothing wrong with it either. But that’s just business, and just one guy, not some giant gay foursome.” He blinked a few times. “Jesus, Sammy. I always… I mean… I had you down as straight missionary position all the way, under the covers, lights off -”

Sam couldn’t hold back a guffaw. “Really, Dean? Come on.” 

“You’re my baby brother! You… you’re not supposed to even know what sex is yet!” Dean blushed. 

“I’m pretty sure we proved differently last night,” Sam smirked.

“You’re just overgrown.” Dean waved a hand. “What’s the weirdest place you’ve ever done it?”

“Uh.” He thought about it for a moment. “There was that cult that kidnapped me. I blew my cellmate there. That weird enough for you?” 

Dean snickered. “First time I had sex was in the ball pit at Plucky’s.” 

Sam felt his stomach roil. “Yeah, I remember that. I had to watch part of that.”

“It’s a beautiful and natural act.”

“Nothing is beautiful and natural about watching your brother do that in there when you’re ten, dude.” He shook his head. “That was scarring.” 

“It was a vital part of your education, Sammy.” 

Sam looked up at Dean, ready to argue, but he stopped himself. Dean was grinning. He wasn’t smirking, he wasn’t sneering, he didn’t have that tight, fake smile he had so often lately. It was just a grin, the normal, natural kind of grin that Sam hadn’t seen on his brother in - well, since he’d gone to Hell. 

Sam grinned back.


End file.
